Anthony my friend, you have no clue about the mind set of a top player/gambler like Alex. Sorry to be so blunt. I will tell you this, it isn't about supporting a family or living comfortably either. Alex is chasing that ever elusive "big score" which never seems to be enough when it does come.
He probably has had enough money several times to kick back and enjoy a modest life style, but that's not where he's at by any means. Alex is a dream chaser and an inveterate gambler, who wants to play in the biggest game he can. Whether it's pool, poker or fighting cocks. He's chasing a thrill as much as anything else. It's like a drug and you can't get enough.
For most of us "normal" people, you could retire successfully in the Philippines with a hundred grand. A nice apartment is $200 a month, and you can live good on much less than a thousand a month. That's why so many retired military guys live there. They can do it on their small pensions, where they couldn't do that here.
Alex is so far removed from the above mind set, that I don't think he could even relate to it in any way. I'm sure that he helps out Phoebe and the kids (who live in Hawaii) when he can. But from what I've heard he is deep in debt. It's not easy to dig your way out of that hole. You need to make that "one big score."